Selling on the Inside: Attitude and Aptitude

By, Troy Waugh

Becoming an insider and selling to owners, board members and top management takes a unique combination of both attitude and aptitude. An attitude that you, as a businessperson, have the expertise and stature to converse with these top officers is crucial. But attitude is not enough. With a proper sense of self-worth you can start the conversation, but it takes real know-how to hold the attention of top officers.


In order to operate successfully in the boardroom, you must have the self-confidence to know that you are on equal footing with the top officers. My football coach once said, "He puts his pants on one leg at a time, just like you." So you must be prepared to talk on the same level as the top officer. Such an attitude also presumes that you can understand the issues facing the top officers. It means that you are willing to articulate your solutions in such a way so that you can be a change agent in the business relationship.

We are all uncomfortable in the presence of power. Top officers exude power. If you are reticent about networking with top officers, you must push yourself to learn the ropes and overcome your fear. After you have met with a few Chiefs (a common reference to CEO, CFO, CIO and CAO and several other titles), you will begin to relax as you realize they are just like you, but different. The difference is that they have common things they are interested in discussing and have a pattern of operating quickly.

Time is a precious commodity to top officers in businesses. The further up the food chain you move in a company, the more time sensitive your prospects and clients will be. For this reason, you will also need aptitude in dealing with the Chiefs.


People who are unsuccessful selling to top officers waste time, don't tell the whole story and communicate poorly. If you can overcome these faults, you can be very successful selling on the inside of a large enterprise.

Top officers, especially CEOs, have learned to make decisions with very little, albeit critical, information. Their jobs require them to make lots of decisions in a short amount of time.

Many of them fear wasting time with someone trying to sell something. Time is a critical resource for a top officer. Investing her time wisely will enable a Chief to make steady progress toward company objectives. Smart officers avoid wasting time above all else.

Before you meet with a top officer, you must do your homework. You should know about the company and its problems. And, if possible, have other insiders on your side.

Having been sold a bill of goods many times, CEOs are particularly suspicious of a professional who only covers the upside of their service, failing to cover the downside. In his book, Think and Sell like a CEO; Tony Parinello recommends you use a balanced reward equation to communicate your benefits. When you say that your service will save $400,000 in taxes, the CEO is thinking, "And, how much audit risk or extra compliance costs will I have?" You present the upside. His mind immediately jumps to the downside. So, you must give both sides of the equation.

Lastly, communicating with CEOs takes skill. You must learn to cover the bullet points very succinctly and accurately. As you cover the bullet points, use written materials to back up the details. This means you must rehearse your oral communications carefully and edit your written materials so the key elements pop right to the top.

With a little attitude and aptitude, any professional can succeed with top managers, board members and owners.

An innovator of dynamic marketing systems, Troy has more than 30 years of experience in marketing professional services. In 1991, he founded Waugh&CO to serve the accounting profession.

Troy draws on his experience as the National Sales Manager for a major investment firm, the CEO of a publishing company and a manager with Price Waterhouse. Recognized as an industry leader, Troy has impacted clients around the world with his dynamic programs.

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